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Search results; 301 homes in Chestertown

Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 private bathrooms
19–24 Jul
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4.91 out of 5 average rating, 66 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds
27 Jul – 1 Aug
4.97 out of 5 average rating, 285 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds
17–22 Jul
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds
26–31 Jul
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
25–30 Aug
5.0 out of 5 average rating, 243 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed
27 Aug – 1 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds
25–30 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds
15–20 Aug
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds
16–21 Jul
4.96 out of 5 average rating, 138 reviews
Top guest favourite
Home in Worton
Cozy Cape Cod in worton MD
3 bedrooms, 4 beds
2–7 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds
26–31 Jul
4.98 out of 5 average rating, 123 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds
23–28 Aug
4.95 out of 5 average rating, 110 reviews
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds
16–21 Jul
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds
16–21 Jul
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds
13–18 Oct
4.99 out of 5 average rating, 251 reviews
Top guest favourite
Home in Chestertown
Still Waters River House
4 bedrooms, 7 beds
1–6 Sept
5.0 out of 5 average rating, 7 reviews